What happens when a deeply technical introvert ends up leading hundreds of people? In this thoughtful and funny Monktoberfest talk, Joe explores how to manage and communicate effectively when “soft skills” don’t come naturally. From skip-level meetings to culture-building, Joe shares concrete tools for scaling empathy, trust, and communication across large teams — without burning out your emotional energy. Whether you’re a new manager, an engineer eyeing leadership, or someone figuring out how to lead authentically as yourself, this talk is a master class of technical management.

Transcript

Hi everybody. There we go. So as some folks here have been talking a little bit about, oh, you know, my technical skills, not so much, I’ve got these other skills. I think it’s interesting to have somebody talk from the other side of this, where I come from it that I have technical skills, but have crippling anxiety around the soft skills part. So the question is how do you lead several hundred people if you have those kinds of disadvantages. So I’m talking a little bit here about how I got my introverted self to scale up to being able to do that sort of job.

  All right, so let’s all pretend for just a moment that you’re in the sort of position where you’ve got managers reporting to you, so this is sort of a director-shaped role. So you’ve got 20 or more people sort of up to a thousand-ish people reporting to you, so you’re going to empathize with that role for this talk. Some of you might have done those roles. Some of you might want to do one of those roles in the future. Some of you may report in through a structure like that, so being able to think like those people are thinking is sort of a useful exercise.

  Importantly, this is useful if your planning horizon is multiple years. If you’re thinking just a month ahead because you’re in fire-fighting mode or you’re a quarter ahead because that’s how you’ve been incentivized, this approach isn’t going to be such a great fit. So there’s always constraints. Budget is always the first constraint. I have some amount of money that I get to spend and the further up the chain you get, to get to spend that however you want. Like, I could have this many people, I could spend this much on marketing, I could have fewer people, spend more on marketing, so — I can’t risk the business, I can’t do dumb stuff that’s going to get us sued, either by not following guidelines or by breaking a contract somewhere else, there’s stuff that I just can’t do, right?

  And all of the people who work for me all have finite emotional energy. I can’t ask them to do something that would require them to be super-human.

  That doesn’t work in the long term.

  One that I didn’t put on here, because it’s hopefully obvious, but apparently I have to say it, is you can’t do things that are wrong. Like, if you are doing things that cause harm to other humans, like that’s not — that’s a constraint.

  I feel like I now need to say that out loud in certain circumstances. Anyway …

  OK, so this definition of director came up through multiple different years in different companies, but what I like to talk about is directors are trusted by the organization. So the organization trusts them to make decisions on their own. The reason why they’re trusted is that directors know when to not make a decision. They know when to ask for help, they know when to ask Legal for an opinion, they need to know when to go and ask the senior VP to sign off for a thing because they’re going to end up getting on the hook for it with the risk or whatever, but because you trust to ask them for help, you trust them to make decisions that are in their space. In order for them to make those decisions, though, they need context. They need to know why they’re doing things, what you’re doing, for whom, etc., so they could make the local decisions, right?

  So with that comes this responsibility for a particular system. So they own it, I trust them to always know what’s going on in their entire world, they know who to ask if they don’t know, they’re aware ahead of time because they have systems in place if things go wrong and their job is to make sure nobody up the chain is surprised by their set of systems, right?

  All right. So the other big thing is when you become a director, this is really the first time where OK you’re allowed to have feelings, like your feelings are important, but then you need to put them away off the side and what really matters is the business, and this is a huge transition for a lot of people because they’ve always thought, well, you know, like I’m upset about this thing or I’m mad about this person or whatever and once you become a director, like, cool, go be mad over there, and then come back and do your job and I don’t need to, like, tell you to do that. That’s just something you do, and I trust you to handle that and handle your only feelings and whatever. If you need help, you know how to ask for it, you know where to go to get the help, but nobody’s looking out and saying, oh, are you OK today? That stops happening when you become director and that’s kind of a shock for folks. But again, that’s part of the trust thing, right? We trust you to ask for help when you need it.

  So all of this is set up for, like, OK, what are you gonna do about it, then? So if you’re a line manager, so the first time you become a manager, you’ve got four, five, eight people reporting for you, you go in and check in on everybody, you have one-on-ones with them, you find out they’re stuck on this problem, I’m going to get them help, I’m going to get them a mentor, I need to know what their career paths are, like what’s going on in their house, like, oh, my basement flooded and so I have to work from home on Monday, and like, oh, my cat’s sick and my kid has a thing and we’re going on vacation and there’s all this stuff that happens to humans. And if you’re a manager, you can be on top of that, you can be the interface for yes, I understand you’ve got stuff going on in your life, but we need to get some stuff out of you and I need to factor all that in. Doing that for people is exhausting. It’s just —

  [applause]

  It’s so much. And if there is — if you’ve got eight people, you can kind of do it, you can have one one-on-one a day, two on Thursday, and you can kind of manage your way through it, but it takes a lot of emotional energy to just empathize retail skill, to be on top of everybody’s stuff and everybody’s got their own set of Imposter Syndrome, like right now I’m talking to people who’ve done this at larger scale than I have, folks who have similar problems, solved them, etc., but Devon always tells me, just because it’s obvious to me doesn’t mean it’s obvious to everybody else, so I should go ahead and say the thing, so thank you, Devon, for going ahead and pushing me.

  But you know, we take everybody out for lunch and OK, this person is sad and why are they sad and all this sort of thing. Maybe you do two people, maybe you 0 do ten, if you were fantastic at this, if you were a genius, maybe you could do it for 20 people. Most people can’t do that effectively for a team and making the folks who work for you feel like anybody gives a crap about the stuff that is going on in their lives is one of the manager’s most important jobs. If you can’t do that for them, how do you expect them to — I need an extra hour to finish this thing up, can we come in early tomorrow and do this? How do you ask people to give up parts of their lives if you don’t care about their lives?

  All right, so what do we do about that once we become a director, right?

  So instead of thinking about an individual person, we start thinking about teams. Is this team doing OK? And it’s a weird transition to make, from being like on top of all this stuff and, like, oh, I know that Jack’s having this problem or whatever, to I only really need to know about the people that need helicopters to get out of dangerous situations because that impacts the budget, but I do care, is the team doing OK? Like, is their manager wallowing and failing? Is their manager not doing the stuff they need to do? That is really tough to tell, because you don’t talk to the folks that are reporting to this manager, like you don’t see them — like, you see them at an all hands, and they’re grumpy about something, you don’t know if they’re grumpy because they didn’t get enough sleep that night or because their manager is just absent. So how do we deal with that?

  Making sure if it’s mission critical. Like, I can’t find out how they’re doing if I can’t explain to them, here’s what you’re trying to do, here’s why it’s important, here’s how you do it, here’s how we do things together, right? So I have to know their mission.

  And I also need to know if those missions — so if I’ve got five or six teams, I need to know if those teams have missions that will add up together into a program that makes the company money or whatever our company is trying to do, right?

  So thinking of people in chunks like this, this is the org chart way of thinking about them, which is interesting, but it’s not the only way.

  Right? You redo your org chart — hopefully not every year, hopefully you do it every three or four years. Every time you have to do a reorg, it’s a pain. Everybody gets knocked off of their comfort zone, they don’t know what their mission is anymore, you have to contextualize everything and everybody is concerned they’re going to lose their jobs and they don’t work for three months and. So you have to have a good reason, either financially or whatever to do one of these reorgs, so the question is, what else could we do? And it’s tempting for a lot of folks to say, we’re just going to use metrics, we’re going to be able to tell if this team is successful because we measured how much code they wrote or how many bugs got filed or anything you do like that, particularly when you have engineers working for you, is mostly useless.

  Because the engineers control the metrics and they’ll just write themselves a boat. Like, it’s just not — any time you measure — you disturb the actual process, right?

  So metrics are an interesting insight point, but if you actually use them to drive compensation or promotions or anything like that, it breaks everything. And this is something that’s very difficult to explain to people who came through sales organizations in particular. Sales organizations are very metrics-driven, because you can measure their effectiveness, how many dollars did you sell this month? What was your margin? So they believe — often believe that everything can be reduced to a number, and the fact that you won’t reduce everything to a number means you’re just a bad manager.

  Which is sort of the opposite of how we’ve found the world actually works with engineers.

  So, you can use them as insight points, like, is there a problem here? Is this team doing a lot less than other teams? Are they doing less than they used to do? Are they doing more than they used to do? Do they have some insight they can share with the rest of us. So those are the kinds of things metrics can tell you, they usually can’t tell you individual developer bad, individual QR person, good failing, you have to rely on your managers for that.

  But I do find that staff meetings that are run correctly, you can often find if a manager has checked out, not paying attention, doesn’t understand how they fit into the rest of the world, etc. If you have those meetings on a weekly or biweekly cadence, you can usually find managers that are starting to lose their moorings a little bit and get them help early.

  But I love skip levels as a Eck in mechanism. So a skip level meeting for those of you who haven’t seen them, done them, is I talk to somebody who reports to somebody who reports to me, or further down on the chain. So I’m reaching down into the organization to talk to somebody.

  So this is all relatively reactive, though. So this is — I’m gathering data, I’m trying to find out what’s going on.

  This is one way of gathering information, trying to work.

  However, your corporate culture is the stories that get told. These are the things we tell each other about our triumphs and our failures. How we talk about them.

  So for example, Jill came in over the weekend and spent 24 hours over the weekend, like, really saved our bacon and made a diving save for this customer and built this thing and hurray, thanks, Jill. That’s one way of talking about it, the other way of thinking about it is Jill’s management team completely messed up what her priorities were over the last six weeks, she was working on the thing that was not the thing we needed to be worked on and so because of that management failure, Jill wasn’t able to go to her kid’s birthday party.

  So like there’s a difference — so that’s a failure story from a certain perspective instead of a success story.

  And finding the right way to talk about that so that, like, hey, maybe next time let’s plan better. Like, here’s this thing coming up that’s really important, maybe more people on the team could be working on this, ahead of the important thing, so that we can all have some life outside of here.

  All right. All right, so the first thing is, you write down some goals, like, what is our culture in my organization. Who are we? Why are we? How do we do things? Like, do we — are we constantly at an imagine state? Are we trying to plan ahead so we’re never in an emergency? One of the things I like to think about is that the people that have context about what our job is, what our mission is, the people who are supported and are as happy as we can help them to be in our organization, those people who have — who are happy people who have context produce more and I don’t care if they’re producing widgets, if you’re writing software, marketing, whatever, people who have context can make a local decision, feel control over it, feel like they’re empowered to make that decision and they’ll make the right decision which creates a loop in which I trust them more and those people will produce a lot more than people I have to tell what to do every day.

  All right, so I do create some context.

  What we’re doing, why we’re doing it, who we’re doing it for, how they use our work, but for all of these, the question is why. Like, why do we do it that way? Why are these people interested from buying from us? Why do these people use our product? Why, why, why? If you understand the why, then I don’t have to explain my differences as to oh, this customer needs this, this customer needs that, whatever, the people who do the work can intuit what needs to be done without their manager or their director or their VP having to tell them each time.

  This takes a massive load off of the leader’s plate. But it creates a lot of work up front to get correct.

  So if you’re wondering, like, oh, my manager sits around all day, doesn’t do anything, sort of writes some PowerPoints. If they’re doing their job correctly, one of the things they’re thinking about is how do I get folks to understand what we’re doing and why? How do I give them enough context, right? So that doesn’t look very much from the outside. It’s one of those ducks sailing smoothly along the water with their feet madly paddling sort of situations.

  But that understanding of context — people that understand that, those are often the people who we often promote from junior whatever, to senior whatever. The junior whatever people have that understand, are able to understand and explain to others why we should do that. But a lot of that starts from the management team being able to communicate effectively downward.

  Carrie and I did a fantastic job when we started working with me. We basically canceled my calendar and reset the week so that my week was under Carrie’s strategic control. And the way that we did this was every week I would come in Monday morning, I thought about over the weekend what this week was about. What’s my one bullet point for the week? What’s my talking point for the week? What’s this week about? And it would often be a culture thing. It might be a technology I’m thinking about, it might be this trend in the industry, but this thing that maybe, let’s talk about for the week and bounce that off of senior staff meeting, see if they have, oh, think about this or we’re doing a little bit of something over here and this team over there knows about this thing and that helped refine that message early and then we use that throughout the week. So we’d give a little shout to staff, hey, here’s the bullet point of the week, in the Slack, feel free to talk about this, and then whenever I got into one-on-one that week later, and the person I’m talking to doesn’t have anything. This often happens, you have a one-on-one, you have a skip level with somebody and you’re like, hey, what’s going on in your world? And they’re like nothing. Oh, cool. Do anything cool last week? No.

  All right. Your team’s working on this. Are you working on that, too?

  Yup.

1. Well, I’ve got this point that I’m willing to talk about, so you get to the point where you’re talking about your thing to the week and at least you have something to go on so the conversation doesn’t get stuck and everybody often you can pull that into the conversation and find out why it matters to them and it’s the ice-breaker.

  The other thing I like this for is if you’ve got a formal mentorship program at your organization so you go to the mentorship meeting and you have the same discussion, what are you stuck on? I’m good. OK I have time to spend here, I can help you, so this is something that those mentor relationships can talk about amongst themselves, as well.

  So you get the whole organization talking about this, a little bit. It’s not a major thing, it’s not that everybody has to write a paragraph at the end of the week or anything like that.

  It’s just a cadence to translate to some type of give a crap at the end of the week.

  One of the big things is for me anyway, being completely extemporaneous in a conversation with somebody who is not responsive like that is just grueling. Just the amount of energy that it takes is OK, we’ve got a half an hour scheduled and I feel obligated to talk with you because I’ve put it on my day so let’s get to something. So getting productive in that conversation quickly radically reduces the energy from me, so this is one of the things of a trick that worked for me.

  Skip levels we talked a little bit about, but how do you find people to do this with and one way is hey, we find out who’s doing something cool this week? And well, maybe somebody is prototyping something, cool, I want to set that up and have that be the demo, and let me be the learner and have them teach me something.

  One of the coolest things about that is you get to learn from all of these people and if you approach them with this level of humility and interest, you often get great stuff out of them, just from understanding how the rest of the business is working underneath you. Folks that are challenged, so teams that are failing, people that are having issues, etc., when you do skip levels with them it’s a little tougher.

  So one of the things to do is to get a trusted intermediary like maybe your admin is trusted to talk about people without them getting scared. Maybe you’ve got a senior engineer who is somebody that you can trust, give more context about, like we want this team to not fail, could you go talk to this person about what’s going on and report back to me, people that can anonymize for you and be trusted to give feedback without it coming back to them and harming them, like building that trust is very difficult.

  And part of that is because skip levels are scary. You get this email from your boss’ boss, or their boss, like, I want to meet with you on Tuesday and you get this oh, no, is there somebody going to be from HR too? Are we all getting fired? Oh, no, something is horrible. So trying to figure out ways to make that less scary. Like in the invite, this is not scary. This is an opportunity, this is not like, don’t freak out, here are three people you can talk to to trust that, right, or here’s what I want to know about and here’s why, but doing that really early in the email where you ask for the meeting or having your admin explain that, like, can be really important. Because otherwise you lose an entire week’s worth of productivity from this person with them just freaking out.

  So that’s important, so this keep confidence thing, so often when you’re doing a skip level, the person will be like, ah, I don’t want to talk bad about my manager, and I’m like, OK, I’m your manager’s boss, and I need to know. I’ll make sure they don’t know it comes from you. I’m not going to act directly on anything you say, but any insight you can give me is really useful. Oh, well, this person is treating that other person in a way that I don’t think is OK. Here are three examples.

  Ooh, all right, well, let me go and dig into that and see if there’s something I can do about that. Or more interestingly, here’s one of the things that you can do as a leader without your team to try and effect that yourself without me having to solve it. So enabling them to solve their own problem, first of all gets me off the hook. So cool.

  But then that builds a leadership skill that they can use down the road and do other things.

  But that keeping of confidence is and the enabling of local solutions, makes these skip levels actually radically more effective.

  All right, so the next thing for culture transmission that I like to do is to have a really well defined promotion path for folks.

  This seems like one of those touchy-feely things that, you know, HR wants you to do, and they’ll just toss off and it doesn’t matter. This ends up being one of the most effective ways to enforce culture.

  So if down the left you have each different level in your organization from entry level to junior to senior to staff to principal, to you know, whatever, and across the right you’ve got your culture of values, like technical expertise or communication skills or whatever the things are that you’re trying to promote and if you can write down in each one of these boxes, I expect an entry-level person to be able to read an email and understand it. I expect the most senior person to not only write an email but for it to embody our values, I expect it to be world class at being able to convince other people of the thing, right? So going from the entry-level skill to the most senior level in that skill and being able to write that down gives a tool to each one of the managers who’s having conversation with their people. Hey, I think it’s time for me to be promoted from junior to senior. Cool. Let’s look at the sheet. Just because you’ve checked off all of these boxes doesn’t mean we’re going to say yes, but it’s are you working above your level or at level or below level in each of these things. I think your communication skills could use some work, let’s get you to talk in front of people more, etc., so it’s a tool for managers to have these promotion conversations in the context of the culture that you’re trying to create.

  All right. The next thing is whenever there’s a change. So we’re going to do a reorg, we’re going to do a layoff, we’re going to create a new team to do this, we’re going to take on a new segment of customers. Whatever what the big change is, being able to communicate that effectively. So this happens more often than you expect. This framework is really useful, particularly if your leadership team gets used to doing it this way. So the first thing is you start a document, you start a draft of the email with just some bullet points that’s going to go out at the end.

  And this seems completely obvious, but usually what happens if you don’t think about things this way is the email gets written at the end and you’ve forgotten all the stuff that you did along the way to come to the decisions that you came to. If you put the email in the same document that you’re, working on, you can change the email as you go. And it turns out to be one of those completely obvious things that once we started doing it, it made this huge difference.

  The next thing you put in there is frequently asked questions, so this is a place where you brainstorm with whatever’s inside the trusted circle about what questions we expect to get asked. The junior engineers are going to ask about this, the senior engineers are going to ask about this, the people who are worried about that customer are going to ask this set of questions. So you don’t have to publish this entire list of questions that you expect people to ask and the answers to them, but if you’ve thought about them ahead of time now if somebody asks you in an all hands meeting, well, why did you do such and such, well our principles are X, Y, and Z, and this is how we made the decision. And now you look like you’re prepared, you had thought through all the stuff that was going on. You cared what the questions were going to be enough to actually prepare for them.

  And so doing this takes a ton of time, but it helps you to look like you weren’t an idiot, and it helps your manager to not — your managers who are working for you to feel like they weren’t blindsided by a thing and it helps your people to feel like their managers weren’t out of the loop and not consulted, etc.

  So I’ve got this thing here, it’s just a way of thinking about those buckets of people.

  But the groups that aren’t on the org chart, so, like, oh, here’s a manager and their manager will take care of them, but the slices that go through the organization are often the most important ones to think about when you’re doing this.

  So senior individual contributors can be your most effective tools to get the rest of the organization bought in. If they get a little bit of heads up about a thing, if they get an extra hour or two to think about it or a day or two to think about a problem, then by the time you announce about it in an email and the junior person next to them freaks out and goes oh, what does that mean and the senior person can go oh, we’ve heard about this, it’s going to be fine. So getting people throughout the organization that can help you to be OK with the message keeps people in the pocket, keeps them working, keeps them productive.

  So that’s one way of thinking about it. The other way of thinking about it is I care about the junior people and their reactions, I can’t talk to each one of them ahead of time, because I can’t trust a junior person not to blog about a thing before the other person who needed to find out about it. I can trust a director-level person, and so there’s this trust gradient means that I can put trusted people around the organization and use them to help me to deal with people’s feelings early.

  All right, so when you then tell people about the change, particularly people who are in that trusted set, you tell them what’s happening, you tell them whether they’re just being told this is happening or whether they’re being consulted. So do I get to change this, or is it too late? So making sure that the people who are going to be upset that they didn’t get a chance to change it are notified early in the process, is a large part of this calculus.

  And then who can they talk to about it when they want to process their feelings or they want to ask questions or whatever, because they need to know who’s already in the trusted circle, you don’t want them to spill the beans to somebody who’s outside the circle yet.

  And that helps them a lot to do it. All right so we talked about the obvious questions, the people are going to ask, informing people’s managers, and the fact that this allows us to help folks, even though we couldn’t think about each one of them individually.

  All right, so this is just a list of some other things that you may want to transmit using these kinds of techniques. These will work for some organizations and not others. These other things will work for almost any other kind of organization, these are the ones that are more specific to software and blame-free postmortems, people like that, if people can’t tell you why something failed and be honest about it, we’re going to have the same failure over and over again.

  If you haven’t red up on the incident commander approach to deal with problems that happened in your organization, look at that particularly if you’ve got bugs, if that ever happens to you, look up that approach. It’s fantastic.

  Having particularly junior folks have an identified mentor in the organization that is not in their chain of command and figuring out how to get them context and content for those conversations on an ongoing basis.

  Terribly useful, and then we talked about using senior individual contributors and your admins as anonymizers, so folks wants to come to Carrie and say hey, I’m really concerned that Joe seems to be upset about this thing, are we all going to lose our jobs and Carrie can say, oh, somebody told me that … And I can address the concern.

  So that’s another approach to see how you can find people that are trustable in your organization.

  But one of the other things I also like is top find things for juniorses and upcoming individual contributors to be able to get visibility for the things this that they’re doing, an opportunity to show off. The stories that we tell are about that great demo that somebody did because they built a thing that we thought was cool.

  All right. So you may not need much of this in your current role. But if you want one of these leadership roles one day, thinking about how your organization is doing this kind of communication, how they’re building the culture, what the culture is, understanding how that culture is being built, will make you more promotable.

  It makes you one of the people on the inside, one of the people who are part of the conversation, one of the people who are in the room when it happens.

  And that will — like, if you’re on a path to this being a thing that you’re interested in, this is one of the ways to get there, is to care about this stuff.

  All right.

  So taking control of your culture, building it intentionally, having tools to do it that are repeatable, having ways of transmitting stuff throughout the organization that don’t rely on your own personal communication skills, your own personal emotional energy, that’s one of the ways to deal with a team that is more than you handle on a day-to-day basis. Some of this is obvious, well, of course I’m going to delegate, whatever, but thinking about how your job changed from when you were a direct managers, to when you were managing managers, that process of who I am, how do I value my time, how do I go about doing what my actual job is, which is building a team, building a large organization, right? That change in your internal feeling is really hard for folks doing through. It’s tough and very few people get through that unscathed, but thinking about it intentionally rather than just having it happen to you is pretty critical.

  All right, so your feelings might not scale.

  But figuring out what the right thing is and having everybody know what that same understanding what the right thing is, that could scale.

  And that’s it.

  [applause]